Unlocking the Florida Keys

Cathy Winston finds unforgettable characters, tall tales and a unique slice of Jewish history beyond the tropical delights


Southernmost Point market in Key West

There’s something in the air in Key West. The southernmost point of the continental United States has long attracted those with a more relaxed attitude to life — and in its early days, a more relaxed attitude to the law.

A haven for smugglers, wreckers and rebels, that included the area’s Jewish community, whose 200-year story includes its own share of larger-than-life characters.

“Key West has always been a place apart, with its own unique story,” says Arlo Haskell, author of The Jews of Key West: Smugglers, Cigar Makers and Revolutionaries, which traces Key West’s Jewish history from 1823, when a Navy crackdown on pirates saw West India Squadron member Levi Charles Harby become the area’s first recorded Jewish visitor.

A generation later, the community had grown enough to need Jewish newspapers shipped in to Key West, before the B’nai Zion synagogue was established in the 1880s, helped by sea routes connecting the southern tip of Florida with Jewish settlements in New York, Charleston and Savannah, as well as Cuba and the Caribbean.

“It ended up having a very cosmopolitan population,” says Haskell, with a Spanish-speaking Cuban population, English-speaking inhabitants and Jewish immigrants from across the Russian Empire and Romania (who, by a linguistic quirk of the two Romance languages, found it easy to communicate with the area’s Cuban community).

As Key West flourished, so did its Jewish inhabitants, who set up cigar-making factories and other businesses — as well as getting involved in rather more radical activities.

As Cuban activist Jose Marti fought for the island’s independence from Spain in the late 19th century, Key West’s de facto rabbi, Louis Fine, secretly led support and helped provide guns for the eventual Cuban uprising, only years after arriving in the US from Lithuania.

“A whole generation of Jewish men, who were friends and associates in town, had all supported the Cuban rebellion,” explains Haskell. “What first seems like something of a conflict, being a religious leader and a military leader, was actually part of the same pursuit of justice.”

It’s not the last colourful episode in the history of Key West’s Jews either, with tales of cigar barons and saloon owners flouting Prohibition rules. In the 1920s, after quotas came into effect to reduce Jewish immigration to the US, some of the community set up an illegal people-smuggling network through Cuba to help rescue Jews from Europe.

Today, Key West is just as colourful as ever (although doubtless more law-abiding) both on land and on water. The buildings lining the streets are every shade of pastel you could imagine, with flashes of bright yellow from the carriages of the Conch Tour Train puttering through town.

Hopping aboard, guides share stories of those who made their living purely from being Key West inhabitants, earning a percentage of the value of wrecks stricken on its shores.

Or there’s the memorable tale behind the Southernmost Southernmost House; built by one particularly determined woman across the street from the previous Southernmost House (whose owners had refused to sell up) purely to claim the title for herself.

People don’t come much larger than life than long-time resident Mel Fisher, whose treasure-hunting exploits are commemorated in the Maritime Museum bearing his name.

After spending 16 years hunting for the wreck of the Spanish galleon Atocha, which sank in a hurricane off the Florida Keys in 1622, Fisher finally found the fabled treasure ship, still packed with riches.

Now on display in the museum, alongside the story of his long search and background on the Spanish conquest of South America, the artefacts are astonishing; golden plates, jewels and more everyday pieces.

Upstairs, further rooms are dedicated to the history of piracy in the Keys and the Caribbean, as well as slavery and the Cuban Missile Crisis.

If you think the Florida Keys are all about beaches and palm trees, it doesn’t take long to realise just how much else there is to discover. Although needless to say, for white sand, gently swaying palms and an ultra-laid-back vibe, it’s still the perfect destination.

We dropped anchor ourselves at Key West’s Opal Key Resort — the sister resort to Reefhouse Resort in Key Largo, where we spent the first night of our stay — a doubloon’s throw from the museum, with relaxing cool blue colour schemes in the room, a great pool, and downtown Key West on the doorstep.

Just a short stroll from the harbour, it’s easy to get out on to the water yourself. There’s a chance to spot dolphins and snorkel on a boat tour with Honest Eco, in Key West’s first electric-powered charter boat, Squid, which uses solar panels to recharge. Or relax back with a glass on a sunset champagne sail with Sebago Watersports as the horizon turns golden.

Of course there’s far more to the Florida Keys than Key West alone, with the aptly named Overseas Highway linking hundreds of tropical islands like beads on a 113-mile necklace, glorying in names such as Boca Chica Key, Little Torch Key and Fat Deer Key.

Some you pass through almost in moments, others are bigger and better known, but there are countless reasons to stop along the way. Our own trip took us from Key Largo — around an hour from Miami Airport — and Islamorada down to Key West, before returning via Marathon.

One of the biggest draws is the wonderful scenery. Surrounded by the Florida Keys National Marine Sanctuary, protecting 2,900 square nautical miles of water, there are boat trips galore to explore the coast and reefs.

You’ll find everything from tours through the mangroves in a clear kayak at Sugarloaf Key with Get Up and Go Kayaking to a glass-bottomed boat tour aboard Key Largo Princess through John Pennekamp Coral Reef State Park, as well as snorkelling trips from Sundance Watersports on Islamorada.

Visiting several different reefs, the colourful marine life here is almost close enough to touch, while the area is a favourite haunt of turtles who feed on the moon jellyfish that float through the waters.

Save time for fresh fish at Robbie’s of Islamorada on the waterfront beforehand, watching the hungry pelicans challenging the tarpon for titbits, as green iguanas lounge on the jetty. Or in Key Largo, stop in at the Fish House, another of our favourites, for fish with their special matecumbe sauce.

More unexpectedly, two of the most fascinating wildlife experiences in the Florida Keys are on dry land. On Summerland Key, the Mote Marine Laboratory International Center for Coral Reef Restoration runs regular public tours, taking you inside their labs to see the research working to revitalise the reefs (including help from some particularly useful crabs) as well as battling diseases affecting the corals and even helping them to reproduce.

Not far away, the Turtle Hospital on Marathon grew out of a hotel with a sideline in rescuing turtles; it’s now entirely dedicated to helping treat diseased and injured turtles. 

Handily, our own accommodation at Tranquility Bay resort was right next door, with gorgeous beach house-style accommodation and some of the best food in the Keys at its restaurant Butterfly Café.

During the turtle hospital tours, there’s a chance to see the operating rooms, hear more about the dangers affecting the world’s turtles and new innovations to treat them, before meeting some of the permanent and temporary residents.

As many as possible are returned to the wild, and those which can’t be released are found new homes — complete with new names, chosen by the people who originally brought them in.

Snow White had already departed, but Grumpy and Sneezy, plus Tater and Tot were still in residence alongside Mojo, a leatherback turtle weighing over 500lb; one final larger-than-life reminder why the Florida Keys are, simply, unforgettable.

Getting There

A seven night fly-drive holiday to the Florida Keys costs from £2,285 per person with America As You Like It, including return flights from Heathrow to Miami with Virgin Atlantic, seven days fully inclusive car hire, two nights at the Reefhouse Resort and Marina, three nights at the Opal Key Resort and two nights at the Tranquility Bay Beach Resort.

For more information about the Florida Keys and details of individual tours and attractions, visit

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